Andy Dick was adopted as a newborn by a military family, and raised in Connecticut, Pennsylvania, New York, Yugoslavia, and Illinois. Always the new kid in school, he learned that he could make friends fast if he acted crazy. In high school, he was elected homecoming king when he ran on the motto, "Don't vote for a jock, vote for A. Dick". After dropping out of college twice, he joined the Second City troupe in Chicago, and by his early 20s he was performing comedy for low or no pay at open mikes. He worked odd jobs and lived in his car for a while, and became good friends with fellow comic Ben Stiller, leading to Dick's first national exposure on Stiller's short-lived but Emmy-winning 1992 sketch comedy show.

In later TV roles, he played the bumbling son of bumbling spies Don Adams and Barbara Feldon on an ill-advised revival of Get Smart, the weasely cub reporter and office assistant Matthew on NewsRadio, the crazed drama teacher on the high school comedy Go Fish, and a wisecracking office supply clerk on Less Than Perfect. He also had his own Andy Dick Show on MTV, with recurring bits including Anus & Andy, Kid Christ, Question Mark Guy, and Zitty McGee, who wants to be a model but has a bad bout of acne. He spoofed Donald Trump in The Assistant, a satirical reality television show where contestants scrubbed vomit to get their shot at Hollywood success.

In movies, Dick's first major role was in Stiller's Reality Bites. He played the sheriff in the Unabomber comedy Ted, a gay best friend in Advice from a Caterpillar, Olga the Masseuse in Stiller's Zoolander, and Santa's scheming son in The Hebrew Hammer, but it remains that his biggest successes have come on television.

After his divorce, Dick and his ex-wife continued living in the same house to raise their children, and eventually his new girlfriend and his ex-wife's new boyfriend moved in. By the mid-1990s, Dick was widely known to be a heavy drug user. He joined Alcoholics Anonymous in 1997, but dropped out when his AA sponsor and friend Chris Farley died of an overdose. He called in to The Howard Stern Show while doing lines of coke and announced his bisexuality on the air. Six months later, Phil Hartman, Dick's close friend and co-star on NewsRadio, was murdered by his wife. In 1999, Del Close, the long-time overseer at Second City who had been Dick's mentor, died of emphysema. Only weeks after that, Dick went bar-hopping in Vegas with his friend David Strickland, who promptly checked into a hotel and hanged himself with bedsheets. About a month and a half later, Dick smashed his car into a telephone pole while high on cocaine and marijuana, and reportedly tried to run from the scene of the wreck, but was tackled and held by a witness until police arrived.

As all this played out very publicly, Dick became more a punchline than a comedian, the butt of jokes on Saturday Night Live, The Simpsons, South Park, and David Letterman's Late Show. In a court deal to wipe away the charges, Dick went into rehab, after which he claimed to be clean and sober, with his career seemingly back on track.

Still, there is evidence to suggest that all is not well in Dick's world. He reportedly acted "berserk" backstage at a 2006 celebrity roast for William Shatner, licking Farrah Fawcett and Carrie Fisher, then fondling and biting a journalist and offering to supply her with cocaine. In February 2007, he was booted from the set of Jimmy Kimmel Live after groping Ivanka Trump. In July 2008 he pulled down a 17-year-old girl's tank top at a chicken wings restaurant in Murrieta, California. And on 23 January 2010 he was arrested in West Virginia on two counts of felony sexual abuse.